Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl ester → HCID 59146165, compound

HRID 1512832Notes

Reaction equation

HRID 1512832 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([C:11]#[N:12])[CH:10]=1)[NH:7][CH:6]=[C:5]2[CH:13]=O.C1(P(=[CH:34][C:35]([O:37][CH2:38][CH3:39])=[O:36])(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>CC#N>[C:11]([C:9]1[CH:10]=[C:2]([F:1])[CH:3]=[C:4]2[C:8]=1[NH:7][CH:6]=[C:5]2/[CH:13]=[CH:34]/[C:35]([O:37][CH2:38][CH3:39])=[O:36])#[N:12]

Participants

4

Reactant 2

HCID 70670Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl esterHCID 59146047HCID 59146047, compound

Product 1

HCID 59146165HCID 59146165, compoundYield 63.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a mixture of 5-fluoro-3-formyl-1H-indole-7-carbonitrile (D133) (8 g) in CH3CN (80 mL) was added ethyl (triphenylphosphoranylidene)acetate (30 g). The reaction was heated to reflux overnight. After the mixture was filtered, the filtrate was concentrated and purified by column chromatography to afford ethyl (2E)-3-(7-cyano-5-fluoro-1H-indol-3-yl)-2-propenoate (D134) (7 g) as a light yellow solid.

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux overnight
  3. filtrationAfter the mixture was filtered
  4. concentrationthe filtrate was concentrated
  5. custompurified by column chromatography

Sources & evidence

ORD record
ord-b431221c7f2b4a4fbe09d07f30bff1ef
Source dataset
uspto-grants-2012_07
Patent number
US08217028B2

Reaction notes

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